4-Toluenesulfonyl chloride → 5-methyl-1-tosyl-1H-imidazole-4-carbaldehyde

HRID 1681741Notes

Reaction equation

HRID 1681741 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH:7]=[O:8].C(N(CC)CC)C.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O.O.CO>[CH3:1][C:2]1[N:6]([S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH:5]=[N:4][C:3]=1[CH:7]=[O:8]

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 27958875-Methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 150519515-methyl-1-tosyl-1H-imidazole-4-carbaldehydeYield 83.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-methyl-1H-imidazole-4-carbaldehyde (20 g) in N,N-dimethylformamide (100 ml) was added triethylamine (20.5 g) and p-toluenesulfonyl chloride (38 g). The mixture was stirred under ice-cooling for two hours. The reaction mixture was diluted with water (600 ml) and separated organic layer was filtered. The residue obtained was suspended in methanol (100 ml). After being stirred at ambient temperature for two hours, the mixture was cooled and filtered to give 5-methyl-1-tosyl-1H-imidazole-4-carbaldehyde (40.3 g).

Workup

  1. temperaturecooling for two hours
  2. customseparated organic layer
  3. filtrationwas filtered
  4. customThe residue obtained
  5. stirringAfter being stirred at ambient temperature for two hours
  6. temperaturethe mixture was cooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-000d99d3366d40e093149586bdb9cb3f
Source dataset
uspto-grants-1992_12
Patent number
US05173493

Reaction notes

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